Former Annapolis mayor Dick Hillman leads his last hike for Appalachian Mountain Club

By Stephen Pimpo Jr. / Capital Gazette

Dick Hillman directing his group. Hillman led his last hike for AMC after leading for 25 years.

Dick Hillman directing his group. Hillman led his last hike for AMC after leading for 25 years. (By Stephen Pimpo Jr. / Capital Gazette)

Stephen Pimpo Jr.stpimpo@capgaznews.com

Ex-mayor has led close to 250 hikes

Sunday saw the end of an era in Annapolis as Dick Hillman led his final hike for the Potomac chapter of the Appalachian Mountain Club after 25 years of service.

The former mayor of Annapolis has led close to 250 hikes during his time with the AMC and has guided more than 4,300 people over nearly 1400 miles. This last hike was called the "Nooks & Crannies of Annapolis" and, even at age 73, Hillman led a group of 58 explorers on a 6-mile journey through the city he has always called home.

"He's just a natural leader and I think organizing this and connecting people and having fun fits who he is," said his wife, Lisa.

The Hillmans have been prominent figures in Annapolis for years. Dick Hillman was born and raised here and has served the city as a county attorney, as well as working for the state's Department of Housing and Community Development. He also leads walking tours as "Squire Richard," teaching people about the city's history.

His wife spent many years working for the Anne Arundel Health System and currently serves on the boards of the Samaritan House, the Library Foundation and Pathways.

Hillman was elected mayor in 1981 after acting mayor Gustav Akerland committed suicide over financial hardships facing the city. As mayor, Hillman was able to lead Annapolis out of bankruptcy.

Appalachian Mountain Club official Rondi Stearns presented former Annapolis mayor Dick Hillman with an award after he led his final hike for the Potomac chapter of the club after 25 years of service. Hillman has led close to 250 hikes during his time with the AMC and has guided more than 4,300 people over nearly 1400 miles.

Appalachian Mountain Club official Rondi Stearns presented former Annapolis mayor Dick Hillman with an award after he led his final hike for the Potomac chapter of the club after 25 years of service. Hillman has led close to 250 hikes during his time with the AMC and has guided more than 4,300 people over nearly 1400 miles.

But even before then, he was known for being active in the community. He was one of the founding members of the Annapolis Striders in 1978. Through the club, he developed a community that began hiking the White Mountains of New Hampshire.

"Then someone said, 'Why do we only do this in May and June? Why don't we do this all year long?'" he said.

This led to more and more frequent hikes until he eventually joined the AMC and started organizing hikes of his own.

Hillman's hikes have covered all kinds of routes — everything from the Appalachian Trail to Fells Point in Baltimore. No matter the location, he is always trying to show people something new.

By Stephen Pimpo Jr. / Capital Gazette

Dick Hillman leading his hike on Main Street. Hillman led his last hike for AMC after leading for 25 years.

Dick Hillman leading his hike on Main Street. Hillman led his last hike for AMC after leading for 25 years. (By Stephen Pimpo Jr. / Capital Gazette)

"At the end of (the hike) people are going to say, 'Wow, I never knew that was there' or 'I learned something,'" his wife said.

Through the years, Hillman has formed lasting connections with the people on his hikes — like Katie Bacon, who first stared hiking with the Hillmans 20 years ago as a sophomore at American University.

"They sort of turned into a family away from home," said Bacon, who says people have mistaken her for the Hillman's daughter.

People always found Hillman's wry sense of humor particularly endearing.

"His humor doesn't play very well when you're mayor, but it plays great when you're a tour guide," said Brad Davidson, who served on the City Council during Hillman's administration.

Plenty of people on Sunday said Hillman's hikes have had a profound impact on them. He's dismissive of the praise, though.

"It's nice that people have enjoyed themselves, but I don't know if I've changed their lives in any way," he said.

"You wouldn't see it," his wife said, "but they feel it."

Family, friends and colleagues all turned out for Hillman's final hike, including Del. Jim Gilchrist, D-Montgomery, and state Sen. John Astle, D-Annapolis.

"He's just a good guy," said Astle, who ran against Hillman in the 1981 mayoral election. "Great sense of humor. He's a warm, caring person."

The hike ended outside Hillman's childhood home on North Street, where he lives with Lisa to this day. AMC official Rondi Stearns presented Hillman with a certificate to commemorate all his years of service.

"I feel like this is kind of like how some people must have felt when Cal Ripken retired," Bacon said.